Contents
Introduction ............................................3 Product Profiles.......................................4 Ethylenediamine (EDA).........................4 Diethylenetriamine (DETA) ..................4 Triethylenetetramine (TETA) ................4 Tetraethylenepentamine (TEPA) ..........4 Heavy Polyamine (HPA) ........................5 Piperazine (PIP)......................................5 Aminoethylpiperazine (AEP) ................5 Aminoethylethanolamine (AEEA) ........5 Typical Physical Properties ....................6 Ethyleneamines Vapor Pressure vs. Temperature ........8 Viscosity vs. Temperature...................9 Specific Gravity vs. Temperature .....10 Ethylenediamine Aqueous Solutions Freezing Point vs. Composition.......11 Vapor-Liquid Equilibria at 760 mm Hg ................................12 Heat of Solution at 22°C ...................13 Specific Gravity vs. Temperature .....14 Piperazine Aqueous Solutions Freezing Point vs. Composition.......15 Vapor-Liquid Equilibria at 760 mm Hg ................................16 Reactions of Ethyleneamines...............17 Reaction Notes ......................................18 Ethyleneamines Applications ..............20 Major End-Uses....................................21 Lubricant and Fuel Additives..............22 Polyamide Resins .................................23 Asphalt Additives and Emulsifiers.......24 Petroleum Production and Refining....24 Resins and Additives for Pulp and Paper .....................................25 Epoxy Curing Agents............................26 Bleach Activators..................................26 Chelates and Chelating Agents...........27 Metal Ore Processing ...........................27 Surfactants and Emulsifiers ................28 Anthelmintics (Dewormers) ...............28 Fabric Softeners....................................29 Fungicides.............................................30 Textiles...................................................31 Polymers and Elastomers....................31 Other Applications ...............................31 Shipping Data........................................32 Product Specifications..........................32 Product Availability...............................33 Storage and Handling ...........................34 Health Effects ........................................35 Ecological Fate and Effects...................36 Product Safety .......................................37 FDA Status .............................................38 References .............................................40 Emergency Service................................47

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Introduction
he Dow Chemical Company, pioneered ethyleneamines development in 1935, when the company was the first to commercialize production, and has been the acknowledged world leader in the business ever since. Today, Dow manufactures ethyleneamines in two world-scale facilities at its Taft, Louisiana, petrochemicals complex. We are the only producer to use both the ethylene dichloride and reductive amination catalytic processes, thus providing unparalleled flexibility in meeting customer needs. Unexcelled quality – in product, technology, and services – is the byword of Dow’s ethyleneamines business. Another first for the company was receipt of ISO 9002 registration in 1990 for the Taft quality systems. Since then, registrations have been received for raw material quality systems, including those for ethylene, ethylene oxide, and ethanolamines, as well as for domestic and international distribution systems. In 1994, our ethyleneamines business won the Shingo Prize for Excellence in Manufacturing. The award recognizes outstanding achievements in manufacturing processes, quality enhancement, productivity improvement, and customer satisfaction. Helping to drive these evergreen quality programs is Dow’s technology leadership. Dedicated research and development focused on the ethyleneamines production processes has constantly improved product quality. Manufacturing technicians employ advanced statistical process control and zone charting for continuous improvement and reduced variability. Backing them is the in-plant laboratory with dedicated equipment for each of the ethyleneamines covered in this publication. And our applications scientists, unsurpassed in their knowledge of ethyl-eneamine end uses, are always ready to assist customers with their needs. Dow’s worldwide distribution network assures you of a readily available source of ethyleneamines.

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Product Profiles
Ethylenediamine (EDA) (1,2-diaminoethane) is the lowest molecular weight
member of the ethyleneamines family. It contains two primary amine groups and forms a maximum boiling azeotrope with water. H2NCH2CH2NH2 EDA is used primarily as an intermediate in the production of bleach activators, fungicides, chelating agents, plastic lubricants, textile resins, polyamides, and fuel additives.

Diethylenetriamine (DETA) is the second linear member of the ethyleneamines
family. It contains two primary and one secondary amine groups. Compared to ethylenediamine, DETA exhibits a broad liquid range: 207°C (405°F) boiling point at 760 mm Hg and -39°C (-38°F) freezing point. H2NCH2CH2NHCH2CH2NH2 DETA is used primarily as an intermediate to manufacture wet-strength paper resins, chelating agents, ion exchange resins, ore processing aids, textile softeners, fuel additives, and corrosion inhibitors.

Triethylenetetramine (TETA) is a liquid containing linear, branched, and cyclic
molecules. The principal tetramine structures are: H2NC2H4NHC2H4NHC2H4NH2 (H2NC2H4)3N HN NC2H4NHC2H4NH2 H2NC2H4N NC2H4NH2 Linear TETA Tris-aminoethylamine (TAEA) Piperazinoethylethylenediamine (PEEDA) Diaminoethylpiperazine (DAEP) (Bis-aminoethylpiperazine)

The major applications of TETA include epoxy curing agents, and the production of polyamides and oil and fuel additives.

Tetraethylenepentamine (TEPA) is a mixture containing linear, branched, and cyclic molecules. The structures of the major TEPA components are:
H2NC2H4NHC2H4NHC2H4NHC2H4NH2 H2NC2H4NHC2H4N(C2H4NH2)2 H2NC2H4NHC2H4N NC2H4NH2 HN NC2H4NHC2H4NHC2H4NH2 Linear TEPA Aminoethyltris-aminoethylamine (AE-TAEA) Aminoethyldiaminoethylpiperazine (AE-DAEP) Aminoethylpiperazinoethylethylenediamine (AE-PEEDA)

Among the major end-uses for TEPA are the preparation of oil and fuel additives, reactive polyamides, epoxy curing agents, and corrosion inhibitors.

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H2NC2H4NHC2H4OH Principal end-uses include surfactants. commercial piperazine is often sold in aqueous solutions to facilitate handling and storage. Piperazine (PIP) is the simplest cyclic member of the ethyleneamines family. and cyclic ethyleneamines. polyamides. fuel additives. The primary and secondary amine groups. Aminoethylethanolamine (AEEA) is an organic base with unique properties that make it an invaluable intermediate. Note: “mlm” or “mlm” = –CH 2 CH 2 – 5 . fabric softeners. chelates. branched. pharmaceutical preparations. Anhydrous PIP has a fairly high freezing point of 110°C (230°F) and a boiling point of 146°C (295°F) at 760 mm Hg. In addition.Heavy Polyamine (HPA) is a complex mixture of linear. The structures of the principal components contain six or more nitrogen atoms per molecule. HN NC2H4NH2 Major end-uses for AEP include the production of urethane catalysts. one secondary. and asphalt additives. and coatings. Aminoethylpiperazine (AEP) is unique among the ethyleneamines: it contains one primary. together with the hydroxyl group. epoxy curing agents. and asphalt additives. combine the features of an ethyleneamine and an ethanolamine. Since this narrow liquid range makes it difficult to handle. corrosion inhibitors. and one tertiary nitrogen atom. The major end-use applications for HPA include oil and fuel additives. The product has two secondary amine groups. and as an intermediate for the production of triethylenediamine polyurethane catalyst. an anhydrous piperazine is available in flake form.4 °F). AEP has a broad liquid range: boiling point of 222°C (432°F) at 760 mm Hg and a freezing point of -17°C (1. the structures of which can be deduced from the chemistry of manufacture and a knowledge of the structures present in TETA and TEPA. HN NH Among the major applications for PIP are anthelmintics.

micromhos/cm Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.22 10.10(7) < 0.091 0.13 Vapor pressure of the solid Extrapolated.986 1.43 x 10-4 0.46(6) .01 < 0. with decomposition Solid at this condition At 42°C At 130°C Forms hydrate with time 6 .63 x 10-4 10-4 (2) Dielectric Constant at 23°C 13.898 0.31 x (7) (8) (9) (10) (11) (12) 0. 65% Piperazine.65 x 0.952 0.35 .29 12. % by wt 100 100 100(12) 100(12) 100(12) 100(10) 14 100 100 7.24(1) 189.39 .17 .01 < 0.01 6. ˚C 11 .86 0.72 x 10-4 (2) 0.015 1.08 < 0. mm Hg 10.007 0. K1. at 25°C in Water 0.14(3) 86.036(4) 0.43 x 10-4 (3) 0.994 1.877(5) 0.40 0.73 x 10-4 0.24 9. Anhydrous At 42°C/42°C At 130°C/20°C Pour point Ionization Constant. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) (2) (3) (4) (5) (6) Linear component only Typical molecular weight For Piperazine.40 x 0. 65% Piperazine.30(1) 275(2) 86.4(10) — (9) 0.45(6) Vapor Pressure at 20°C.72 — — (9) (9) Solubility in Water at 20°C.14 129.10 103. Anhydrous Aminoethylpiperazine Aminoethylethanolamine Molecular Weight 60.52 0.95 x 10-4 (2) 0.24 0.15 Freezing Point.63 10-4 10-4 7.092 49.32 8.32(6) 41 110 .28 0.21 104.13 19.980 0.030 Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.Typical Physical Properties Apparent Specific Gravity at 20/20°C 0.01 < 0.17 146.01 Electrical Conductivity at 25°C.

heat of fusion 50.13910 . melting point 36°C.65 0. BTU/lb(16) .1193 1.52 0.036 0. °C per mm Hg 0.8 50 mm Hg 47. BTU/lb .9 144 184 236 27 — (9) ∆ Boiling Point/∆p.058 0.5(10) 0.13251 .162(1) .4 140.68 0.457 1.499 1.74 cal/g At 130°C.052 0. cal/g•°C 0.0 Refractive Index.6°C.304 .139(1) — — .3 183 215 279(8) 54 — (9) 10 mm Hg 19.80 7. 750-770 mm.403 .0 83.78(13) 0.1 221.505 1. heat of fusion 72.16 26. °C 760 mm Hg 117.3 100. nD20°C 1.037 0.486 (13) (14) (15) (16) At 42°C.0 206.501 1.3 161.61 0.73(11) 15.12395 Heat of Formation at 25°C.043 0. cP 1.9 277(8) 288(8) — 116 146. melting point 109.64 Heat of Vaporization at 760 mm Hg.0 242.14696 .9 127.045 — 0.63(14) 0.9261 .4 88.14744 .Boiling Point.049 Absolute Viscosity at 20°C.7 22.58 0.483 1.14353 .056 0.14487 . BTU/lb(15) 270 197 162 162 99 528 250 152 237 Heat of Combustion at 25°C.6 134.63 0.8 123.513 — — (9) (9) Specific Heat at 20°C.83 cal/g Estimated from vapor pressure using Clausius-Clapeyron equation Calculated from gross heat of combustion 7 .569 .1 460.256 .14643 .

˚C 8 . Vapor Pressure vs. mm Hg 100 80 60 50 40 30 20 10 8 6 5 4 3 2 EDA 65% PIP DETA AEP AEEA TETA TEPA UHP HPA X 1 -20 0 20 40 80 120 160 240 320 Temperature. ˚F 0 1000 800 600 500 400 300 PIP 200 20 40 80 120 160 200 240 320 400 480 560 Vapor Pressure.Figure 1: Ethyleneamines. Temperature Temperature.

0 65% PIP PIP 0.0 Viscosity.0 HPA X 1000.Figure 2: Ethyleneamines.0 EDA 1. Viscosity vs.0 AEEA TEPA UHP 100. cP TETA AEP DETA 10.1 -50 0 50 100 Temperature. Temperature 10000. ˚C 150 200 250 9 .

75 -20 20 60 100 140 180 220 260 Temperature.85 0.00 AEP TETA DETA Specific Gravity. Temperature 1. Specific Gravity vs.90 TEPA UHP PIP 0. t˚C/20˚C 0.95 EDA 0.Figure 3: Ethyleneamines.05 AEEA 65% PIP HPA X 1. ˚C 10 .80 0.10 1.

Freezing Point vs. Composition 15 5 Eutectic -0.8˚C -5 Temperature.0˚C -55 0 10 20 30 40 50 60 70 80 90 100 Composition. ˚C -15 -25 -35 -45 Eutectic -53.Figure 4: Ethylenediamine Aqueous Solutions. Weight % Ethylenediamine 11 Composition of Monohydrate Composition of Dihydrate .

Mole % Ethylenediamine 12 . ˚C 112 108 104 100 0 10 20 30 40 50 60 70 80 90 100 Composition. Vapor-Liquid Equilibria at 760 mm Hg 120 Vapor Phase 116 Liquid Phase Temperature.Figure 5: Ethylenediamine Aqueous Solutions.

Figure 6: Ethylenediamine Aqueous Solutions. Heat of Solution at 22˚C 50 45 40 35 -∆ Hm. cal/gm of Solution 30 25 20 15 10 5 0 0 10 20 30 40 50 60 70 80 90 100 Composition. Weight % Water 13 .

94 0. Specific Gravity vs.98 0. Weight % Ethylenediamine 14 .92 0.Figure 7: Ethylenediamine Aqueous Solutions.90 0.88 0 10 20 30 40 50 60 70 80 90 100 Composition.96 Specific Gravity at 20/20˚C 0. Temperature 1.00 0.

% piperazine Composition of Hexahydrate 15 . Weight % Piperazine Studies show evidence of a metastable freezing point in the region of 20 wt. Freezing Point vs.2˚C 20 0 Eutectic -1˚C -20 0 10 20 30 40 50 60 70 80 90 100 Composition.Figure 8: Piperazine Aqueous Solutions. Composition 120 100 80 Temperature. ˚C 60 40 Eutectic 33.

Vapor-Liquid Equilibria at 760 mm Hg 150 145 140 135 Vapor Phase 130 Temperature. Mole % Piperazine 16 . ˚C 125 Liquid Phase 120 115 110 105 100 95 0 10 20 30 40 50 60 70 80 90 100 Composition.Figure 9: Piperazine Aqueous Solutions.

Other ethyleneamines react similarly.Reactions of Ethyleneamines† † Illustrated by reactions of ethylenediamine (EDA). 17 . depending upon structure.

.Alcohols and Alkylene Glycols Simple aliphatic alcohols can be used to alkylate ethyleneamines with hydrogen in the presence of a reductive amination catalyst (17). an explosive compound. RX 4.Ureas Ethyleneamines react with urea to form substituted ureas and ammonia (11). . forming crystalline. Various diamides of EDA are prepared from the appropriate methyl ester or acid at moderate temperatures (2. RX 5. RX 7. . . RX 2. Ethylenedinitramine. Product distribution is controlled by the amine-to-epoxide mole ratio.Aziridines Aziridines react with ethyleneamines in an analogous fashion to epoxides (15-16). Monoamides can be cyclized to form imidazolines. to form mixtures of hydroxyalkyl derivatives (12-14). water soluble salts.Organic Acids Ethyleneamines react with acids.Nitriles Hydrogen cyanide (HCN) and aliphatic nitriles (RCN) can be used to form imidazolines (9-10). or acyl halides to form amidoamines and polyamides. .Epoxides Ethyleneamines react readily with epoxides. . Product distribution is controlled by the ethyleneamine-to-aziridine mole ratio.Inorganic Acids Ethyleneamines react vigorously with commonly available inorganic acids. RX 6. is made by reacting one mole of EDA with two moles of nitric acid and splitting two moles of water from the salt at elevated temperatures (1) . This can be done without isolating the monoamide (4-8). esters. RX 3.3). acid anhydrides. Either gas.Reaction Notes RX 1. .or liquid-phase reactions of ethyleneamines with glycols in the presence of several different metal oxide catalysts lead to predominantly cyclic ethyleneamine products (18). 18 .

crosslinked. H2O.RX 8. they are sufficiently reactive that upon exposure to adventitious water. . metal complexation or choice of solvent. react with ethyleneamines to form various polymeric. Carbon dioxide reacts readily with EDA in methanol to form crystalline N-(2-aminoethyl)carbamate (23). RX 9. .and disubstituted imidazolidines via cyclization of the intermediate Schiff base (21). N-Alkyl-piperazines and piperazine can react with nitrosating agents. or nitrous acid. Aliphatic dihalides. carbon dioxide. nitrites. The products depend on stoichiometry. which can be reacted with zinc (or manganese) to give the appropriate dithiocarbamate salt. NOx. reaction conditions. Ethyleneamines are soluble in water. react with ethyleneamines to form mono. the reaction being mildly exothermic.Sulfur Compounds EDA reacts readily with two moles of carbon disulfide (CS2) in aqueous sodium hydroxide to form bis sodium dithiocarbamate. depending on the reactant ratio (20).Halides Alkyl halides and aryl halides. nitrogen oxides. such as ethylene dichloride. O2 Under normal conditions ethyleneamines are considered to be thermally stable molecules. water-soluble cationic products or higher ethyleneamine products.Aldehydes Ethyleneamines react exothermically with aliphatic aldehydes. and oxygen. and structure of the ethyleneamine. to form nitrosamine derivatives (24). Reactions of aldehydes with such ethyleneamines as EDA or DETA give mono. RX 10. The hydrates of linear TETA and PIP melt around 50°C (25-26). RX 11. trace levels of byproducts can form and increased color usually results. Mixing methylene chloride and EDA reportedly causes a runaway reaction (19). .Environmental Reagents: CO2. However. amine hydrates may form. . However. Ethylene thiourea. 19 . a suspect human carcinogen. Product distribution is controlled by reactant ratio. activated by electron withdrawing groups.or disubstituted derivatives. such as nitrogen oxides. is prepared by reacting CS2 in aqueous EDA (22). in concentrated aqueous solutions.

The following table lists the major end-use applications for these versatile materials. basicity. and surface activity. .Ethyleneamines Applications Ethyleneamines are utilized in a wide variety of applications because of their unique combination of reactivity. They are predominantly used as intermediates in the production of functional products.

Major End-Uses for Ethyleneamines Application Lube Oil Additives Fuel Additives Polyamide Resins Asphalt Chemicals Corrosion Inhibitors Wet-Strength Paper Resins Epoxy Curing Agents Bleach Activators Chelating Agents Ore Flotation Agents Surfactants Fabric Softeners Fungicides Anthelmintics Spandex Fibers Urethanes Military Decontamination Agents Plastic Lubricants Ion Exchange Resins Coatings NOTE: The largest volume applications are indicated by ++ EDA DETA TETA TEPA Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine HPA PIP AEP AEEA Heavy Polyamine Piperazine Aminoethylpiperazine Aminoethylethanolamine EDA DETA + TETA + + ++ + + ++ TEPA ++ + ++ + + + ++ HPA ++ PIP AEP AEEA ++ ++ + + ++ ++ ++ + + ++ ++ + + ++ + + ++ ++ ++ + + ++ ++ ++ + + ++ + + + ++ ++ + + + ++ 21 .

a different linkage is employed in another important class of ashless dispersants – the Mannich bases (60-70). by solubilizing oil-insoluble liquids. and by neutralizing acidic species formed in the combustion process. The ethyleneamine derivatives most commonly employed for these tasks are the mono.and bis-polyisobutenyl-succinimides. varnish inhibitors for lubricating oils for twostroke engines (59). normally prepared by the condensation reaction of polyisobutenyl-succinic anhydrides (PIBSAs) (1. 22 .Lubricant and Fuel Additives The largest application area for ethyleneamines is in ashless dispersants for engine oils and other lubricants. Post-treatments of the succinimides are commonly utilized for performance improvement in engine oils (4658). They are prepared on a commercial scale by reaction of an alkylphenol with formaldehyde and an ethyleneamine (71-76). Besides the more common means of linking long-chain hydrophobic moieties to ethyleneamines via the succinimide linkage. The higher molecular weight ethyleneamines are most popular for these derivatives. 2) with ethyleneamines (3-44). all the ethyleneamines have been employed for various products (45). The alkyl and ethyleneamine moieties are similar to those used in the succinimide products. The lubricant additives function mainly to reduce the formation of however. Ethyleneamines are also used in dispersant- sludge and varnish deposits within internal combustion engines by inhibiting the aggregation of particles. and in certain dispersantdetergents for fuels.

Being soluble in alcohol-based solvents and exhibiting outstanding adhesion to polyolefins. Polyamide Resins The main polyamide resin type. cellophane. 23 . Anti-rust additives for lubricating oils have also been prepared by reacting ethyleneamines with fatty acids followed by reaction with polyalkylenesuccinic anhydrides (77. a number of antiwear/antiscuff additives for lube oils and greases also use ethyleneamines. Oil additives providing detergent properties have also been prepared from ethyleneamines (79. and foil webs (8). and paper. DETA. and AEEA have found significant commercial application as dispersant detergent additives for gasoline when made by this route. and. for example. to provide a reaction site. These polyamides are used in hot-melt.Lubricant and Fuel Additives (cont’d) Additives for lubricating oils providing a combination of viscosity index improvement (VII) and dispersancy have also been reported. tri. Dispersant-detergent additives useful in gasoline are prepared by the direct alkylation of ethyleneamines with chlorinated polybutenes (81-86). EDA is a principal amine reactant (1). plastic. These additives are prepared from ethyleneamines by reaction with various viscosity index improvement polymers that have been modified. abrasionresistant.and polybasic fatty acids. EDA. 4). 78). in addition to the liquid resins used as epoxy hardeners. and metal. They are also used in preparing fatty acid/amine soaps and poly(urea) thickeners for lubricating greases. overprint varnishes. paper. They are also used to modify alkyd resins in certain thixotropic coating systems (5). PIP and certain PIP derivatives are used with EDA in certain cases (3. Cetane improvement in diesel fuels has been reported for a mixture containing EDA (96). via chlorination. polyester. they are particularly suited to these applications. film. is that prepared generally by the condensation reaction of diamines with di. Polyamide resins find wide use as binders in printing inks for flexogravure application on certain paper. to plasticize nitrocellulose lacquers (6). Thermoplastic polyamides are similarly used in formulating glossy. and heat-seal adhesives for leather. Numerous similar products made generally by alkylating or acylating EDA or DETA (87-95) are also used as fuel detergent and deposit control additives. 80). however.and tetramines are sometimes used at low levels to achieve specific performance (2). and as corrosion inhibitors in alkyd paints (7). pressure-sensitive.

and bis-amidoamines. patching.and bis-amidoamines.Asphalt Additives and Emulsifiers Mono. demulsifiers. Specific ethyleneamine derivatives can also be used for water clarification (16. neutralizers. Petroleum Production and Refining A number of ethyleneamine derivatives are also employed in petroleum production and refining operations as corrosion inhibitors. 24 . 12. to separate alkenes from thermally-cracked petroleum products (20). and TETA. to separate carbon disulfide from a pyrolysis fraction (21). and their mixtures are used in antistrip formulations and asphalt-in-water emulsions. for example. They generally utilize the condensation reaction products of higher ethyleneamines and fatty or dimer acids. mono. and surfacing. and pH and increase resistance to hydrolysis (15). Antistrip additives promote adhesion between the mineral aggregate and the asphalt in mixtures for road paving. Similar ethyleneamine derivatives are used to make stable asphalt-in-water emulsions (8-16). as part of a system used to extract thiols from petroleum distillates (18). The oil-water emulsions generated at times by petroleum wells can often be broken with certain ethyleneamine derivatives (8-10) (EDA. i. Typically. Corrosion inhibitor formulations for downhole petroleum production applications use a significant volume of ethyleneamines. Ethyleneamines are also employed in petroleum refining operations. 17). They are usually applied to the petroleum well by any of several methods designed to create a film of inhibitor on the surfaces of the steel structures in the petroleum well. These are generally used as their HCl or acetic acid salts. imidazolines. and in the processing of certain catalysts (22-25). In some secondary recovery operations.e.. 13). TEPA and other ethyleneamines combined with thickeners help stabilize viscosity. mobility. ethyleneamines can be used to decrease the migration of injected chemicals into the formation by adsorption and precipitation (14). 11. imidazolines. as part of a composition used as an antioxidant to control fouling (19). These films displace the corrosive production fluids and attract a film of petroleum which further isolates the steel from the fluid. and functional additives. DETA. and polyamides. they are represented by the products made from DETA and fatty acids (1-7). They are typically prepared from the higher molecular weight ethyleneamines and fatty acids (1-7).

rather than the Certain pigment retention and drainage additives made with ethyleneamines include various polyamides (10. 2). incorporate ethyleneamines such as DETA. are also used. The most popular paper wet strength resins are the modified polyamides typically made with DETA. adipic acid and epichlorohydrin (37). These resins can be used under less corrosive neutral or alkaline conditions. The sulfur-free delignification of wood chips with EDA-soda liquors has received some interest in the past few years (22-24). and paper coatings (21). antistatic agents (17-20). 8). represent a major end use for ethyleneamines. The cationic formaldehyde resins. Even though they tend to be less expensive. made by the reaction of ethyleneamines with epichlorohydrin (9). Cationic formaldehyde. waterproofing and sizing compounds (14-16).and melamine-formaldehyde types (1. 11) and polyamines (12). and polyamine resins. The bis-amide made by reacting EDA with stearic acid. 25 . ethylenebis(stearamide). and/or TEPA in the resin backbone to provide substantivity to the cellulose fibers in paper. TETA. both urea. and acidic conditions required by modified formaldehyde resins. toweling. Polyamine wetstrength resins. is used as a defoamer in paper mill operations. packaging paper products. Improved rates of EDA recovery (25) have also been developed for EDA-sulfide pulping processes (26. polyamide. 27). 6. to make nonacidic papers. added to the beater stock to improve the wet strength of tissue. these types of paper wetstrength resins have been decreasing in popularity due to the adverse health effects associated with formaldehyde. Numerous modifications of this resin type have been reported (4.Resins and Additives for Pulp and Paper Ethyleneamine-based chemicals are used widely in the paper industry to impart specific functional characteristics to the finished paper. Ethyleneamines are also used in the preparation of certain flocculating agents (13).

castings. ketimines. to DETA (2) as shown above. 7). to give derivatives providing longer pot life and better wetting of glass (14). which is then reacted with two moles of acetic anhydride to form the tetra-amide. cyanoethylation. Other modifications of the ethyleneamines include partial reaction with epoxy resin to form a prepolymer. Bleach Activators Tetraacetylethylenediamine (TAED) has been widely adopted for use in home laundry products as an activator for peroxygen bleaches. usually by reaction with acrylonitrile. and a variety of other ethyleneamine modifications (15-18). etc. such as ethylene oxide. and safety improveAmidoamines and reactive polyamides prepared by condensation of TETA or higher polyamines with fatty acids (3-5) and dimer acids (6. respectively. laminates. and a polyamine. 26 . made by the reaction of EDA with acetone. adhesion. patibility with liquid epoxy resins (9-13). Most of the amidoamines and reactive polyamides contain significant levels of imidazoline structure. grouts. It is prepared by first reacting EDA with two moles of acetic acid to form the bis-amide. adhesives. formaldehyde. (1). For example. Although the ethyleneamines themselves are often used as the curing agent or part of a curing agent package. and solvent resistance (8). a common modification is the addition of an alkylene oxide. handling. The presence of different polyamino functionalities in the higher ethyleneamines allows partial reaction with various modifiers while retaining sufficient primary and secondary amino functionality for reaction with the epoxy resin portion of the system. are widely used for longer pot life and better flexibility. they are commonly modified in various ways to achieve performance. Mannich bases prepared from a phenol. and tertiary amino functionality to catalyze that reaction.Epoxy Curing Agents All the commercial ethyleneamines are used either neat or as derivatives for curing epoxy resin-based coatings. which provides improved com- ments.

or need to be buffered. 2). These derivatives selectively adhere to silica particles and permit their removal by flotation procedures (1. The most important commercial family of chelating agents is ethylenediamine tetraacetic acid (EDTA) and its various sodium salts. and nickel from their sulfide and oxide ores (4). has found application recently in chlorine-free paper pulp bleaching to prevent iron from decreasing efficiency of the hydrogen peroxide (6). such as electroplating and electroless metal coating with specific metals and many alloys. They may be made also by reaction of the ethyleneamine with sodium chloroacetate. called chelates. where their metal complexing properties are required. This property makes the ethyleneamines useful in specialized applications. These same kinds of derivatives can be used for beneficiation of niobium and tantalum ores (3). and the ethyleneamines themselves aid extraction of copper. made from EDA. and in lead ore processing and recovery operations (5-8). The intermediate polynitrile may either be hydrolyzed in situ (3). Chelating resins. 8). Diethylenetriaminepentaacetate (DETPA). such as zinc and copper. and formaldehyde in the presence of sodium hydroxide (1. with most di. 5). and as ingredients in systems for etching and for stripping nickel and nickel alloy coatings. polymers (7. separated. 2). sodium or hydrogen cyanide. or separated and hydrolyzed separately (4. They operate by forming stoichiometric complexes. made from DETA. or transported. and fibers (9) have also been developed. Metal Ore Processing Certain processes for enrichment of iron and phosphate ores use amidoamines and imidazolines made from ethyleneamines and fatty acids.Chelates and Chelating Agents Polycarboxylic acids and their salts derived from ethyleneamines are used in a variety of applications where specific metal ions interfere with processing. concentrated. 27 . AEEA and DETA are also used to make similar polyacetic acid or acetate products. chromium. It should be pointed out that unmodified ethyleneamines also form stable complexes with certain metal ions. These compounds are produced on an industrial scale primarily through the reaction of the ethyleneamine.or polyvalent metals.

amine salts or soaps obtained by simply mixing the amine with a fatty acid (1. and the imidazoline formed by the reaction under vacuum at virtue of their mildness and good foaming characteristics. The imidazolines are generally converted into amphoteric surfactants for this application by reaction with one or two moles of sodium chloroacetate (9-11).Surfactants and Emulsifiers To prepare surfactants derived from ethyleneamines. The PIP salts have long been the agents of choice for use against roundworms and pinworms (1). amidoamines derived by the non-cyclicizing reaction between amine and acid. 28 . or TEPA and fatty acids also function as water-in-oil or oil-in-water emulsifiers (12). 2). The products of a reaction between DETA. elevated temperature to remove two moles of water are all used. A variety of 2-alkylimidazolines and their salts prepared mainly from EDA or AEEA are reported to have good foaming properties (3-8). TEPA. Anthelmintics (Dewormers) Piperazine is the active ingredient in certain veterinary anthelmintic preparations – primarily for combating intestinal worms in poultry and swine. ethoxylated with an average of 17 moles of ethylene oxide. improves the soil antiredeposition and clay soil removal properties of certain liquid laundry detergents (13). AEEA-based imidazolines are also important intermediates for surfactants used in shampoos by TETA.

generally with dimethyl sulfate. As a result. Softeners also act as antistatic and antisoiling agents. that are either cyclized to the corresponding imidazoline by further dehydration. to yield compounds that can be formulated into softener products for home laundry use (4-6). These intermediates are then quaternized. Softeners are added to the home washing machine during a rinse cycle or as part of a detergent/softener combination product. they have gained some popularity where environmental biodegradation concerns outweigh their The most common ethyleneamine-based fabric softeners are bis-amidoamines. 2). 29 . Softeners based on bis-imidazoline compounds are also prepared by condensing TETA or TEPA with fatty acids (7) or triglycerides (8).Fabric Softeners Softeners are commonly added to textile materials to make them less harsh. such as AEEA. and impart fluffiness. The amino esters. are more subject to hydrolysis than the amidoamine and imidazoline compounds. or to the clothes dryer. or reacted with ethylene oxide (3) to convert the central secondary amine group to a tertiary amine. decreased storage stability and performance. Softening agents based on DETA and TEPA are also used in industrial textile processing operations (1. “softer” or more pleasing to the touch. or sodium chloroacetate. followed by quaternization with dimethyl sulfate. which gives amphoteric softeners (9). as well as their quaternized derivatives. made from DETA and fatty acids. Amino esters are made from acids and an amino alcohol.

A 2:1 EDA-copper sulfate complex has been suggested for control of aquatic fungi (10). was found to be unstable. Zineb and maneb are normally formed by the addition of zinc or manganese salts to nabam solutions. it is stabilized by conversion to certain other divalent metal salts. preventative. rust. contact fungicides first used in the early 1940’s. The ammonium (amobam) and mixed zinc and manganese (mancozeb) salts are also known. primary commercial products. 30 . The most important of the imidazoline type (8) is 2-heptadecyl-2-imidS CH2–NH–C–S–Na H2C–CH2–CH2–NH2 + CS2 + 2NaOH CH2–NH–C–S–Na S + 2 H2O This sodium derivative. and blight. prepared from EDA and stearic acid. nabam. and grain crops for prevention of mildew. They are used on many fruit. vegetable. scab. The zinc (zineb) and manganese salts (maneb) are especially effective (1-7) and are today the azoline (9). The EBDCs are prepared by reacting EDA with carbon disulfide in the presence of an aqueous base. potato. However.Fungicides The ethylenebisdithiocarbamates (EBDCs) are a class of broad-spectrum. Other materials based on EDA have also been suggested as fungicides. It is used as the acetate salt for control of apple scab and cherry leaf spot.

plaster systems. in phenolic resin curing. and they are used in styrene-butadiene latex processes to coagulate the low levels of finely-dispersed particles in the reaction medium (12-15). and polyol starters. TETA. functional fluids. and mothproofing (7). and as a parting material. shrinkproofing wool (5). gas and water treating. to inhibit isoprene polymerization. and for etching polyimide films. preservative. They include coal-oil emulsification and coal extraction. Urethane systems and processes employ certain ethyleneamines and their derivatives as curing agents. Other Applications Ethyleneamines find application in numerous other specific industries. and surface gloss enhancer.Textiles Ethyleneamines are used in the textile-related industries for a variety of applications. Dye assist compounds for synthetic fibers have been derived from EDA. DETA. static prevention (6). EDA specifically can be used as a stabilizer for certain urea resins. including the treatment of a wide variety of natural and synthetic fibers for modification of certain properties (1. 31 . catalysts (TEDA [triethylenediamine] is a significant example). TETA has been recommended as a curing agent for furfural resin binders in foundry molds and molded graphite. The bisamidoamine condensate made from TETA or TEPA and stearic acid is used as a defoamer in certain textile treatment baths. and TEPA (8-10). explosives. Ethyleneamines find application in vulcanization processes for certain rubbers (1-11). petroleum production. 2). EDA is used in preparing silane and silanol compounds that improve the adhesion between inorganic surfaces and polymer films. as precursors for certain compounds providing durable press (3). to reduce static in polystyrene foam. and membranes. Acrylate and other monomer vapors can be efficiently removed from vent streams with scrubber solvents containing TETA. stone and concrete coatings. EDA reacted with stearic acid makes ethylene-bis(stearamide) (EBS) that is used as an external lubricant for ABS resin and PVC. fire retardants. pharmaceuticals. Polymers and Elastomers EDA is a key component of the polymer in spandex fiber. DETA is a component of Nylon 6 (11). ceramics. polymer concrete and concrete additives. industrial corrosion inhibition. light stabilization of spandex fibers (4). ion exchange resins. viscosity regulator.

95 8.30 8.51 7. 65% Piperazine.984 1.48 7. Please contact Dow at the numbers on the back of this booklet. lb Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 7.Shipping Data Since governmental regulations are subject to change.92 8.21 8.980 0.60 Metric Units Average Weight per liter. kg Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 0. additional information on shipping data. Average Weight per gallon.27 8. 65% Piperazine.005 (1) — (2) 0.011 1. We will provide a technical contact to discuss specific questions you might have.896 0.900 0.977 0.56°C 7.953 0.995 1.18 8.47 — (2) — (2) 8.56°C 0.027 (5) At 80 °C at 15.015 — (2) — (2) 0.39 (1) — (2) 8.15 8. 32 .57 (5) At 80 °C at 15.991 1.24 8.987 1.44 8.031 Product Specifications Product specifications and methods are available upon request. labeling and container requirements may be obtained by contacting Dow at the numbers on the back of this booklet.949 0.

00623 (3) 0.00106 0.∆lb/gal/∆t 10°C to 30°C. per °C at 20°C 0. rail car.00081 0.00081 0.00640 (3) Coefficient of Expansion.00086 0.000842 0.00086 0.00661 0.00095 (5) — (2) 0. ASTM Method D 1310 Product Availability Products are available in bulk ocean tanker.00110 0.00085 0.00092 0. and nominal 55gallon drums. ASTM Method D 92 TO = Tag Open Cup.00642 (3) 0.00077 Flash Point (6). per °C at 20°C 0.00077 at 55°C 0.00110 0.00076 — (2) — (2) 0.00703 0.00080 0.00076 0. °C Closed Cup 43 T 98 P 149 P 171 P 174 P None T 54 P 102 P 127 P Open Cup 39 TO 107 C 154 C 182 C 229 C 96 C 102 C 121 C 154 C (6) T = Tag Closed Cup. 33 .00083 0. per °C 0.000815 (3) 0. °F Closed Cup 110 T 208 P 300 P 340 P 345 P None T 130 P 215 P 260 P Open Cup 103 TO 225 C 310 C 360 C 445 C 205 C 215 C 250 C 310 C (6) T = Tag Closed Cup.00076 0.000951 0.00106 0.00787 (4) — (2) 0.00083 0.00095 (5) — (2) 0.00081 0. per °C 0.00077 at 55°C 0.00085 0. ASTM Method D 56 P = Pensky-Martens Closed Cup.00077 Flash Point (6).000943 (4) — (2) 0.00080 0.000747 (3) 0.00089 0.00081 0.000767 (3) Coefficient of Expansion.00794 0.000792 0. tank truck. ASTM Method D 56 P = Pensky-Martens Closed Cup.00076 — (2) — (2) 0.00092 0.00680 (3) 0. ASTM Method D 1310 ∆kg/liter/∆t 10°C to 30°C.00089 0. ASTM Method D 93 C = Cleveland Open Cup. ASTM Method D 92 TO = Tag Open Cup.000769 (3) 0. ASTM Method D 93 C = Cleveland Open Cup.

Consequently. Water. valves. Carbon steel transfer lines or agitated equipment will suffer enhanced corrosion because of erosion of the passive film by the product velocity. However. Recommended gaskets for ethyleneamine service are made of GRAFOIL™ flexible graphite or polytetrafluoroethylene (TFE). However.001 in/yr) at typical storage temperatures. Carbon steel is not recommended for EDA. Ethyleneamines can permeate polyethylene and polypropylene. or be thoroughly wetted with water and then disposed of in closed. for nonaqueous. 34 . Modest storage temperature (less than 60°C) and nitrogen blankets will allow the use of carbon steel. e. TFE is an alternative to elastomers since it is resistant to ethyleneamines. since TFE is not a true elastomer. porous insulation may introduce the hazard of spontaneous combustion if the insulation is saturated with ethyleneamines from a leak or external spill. Galvanized steel. No single elastomer is acceptable for the entire product line. Risk of insulation fires can be reduced by insisting on good housekeeping. except EDA. in dedicated service. or AEEA storage tanks. Most commonly used industrial thermal insulating materials are acceptable for ethyleneamine service. To avoid this situation. spill absorbents and metal wire mesh (such as that used in vapor mist eliminators). this may lead to spontaneous combustion. maintenance of weather barriers. minimizing insulated flanges and fittings. then 300 series stainless steels are recommended for the storage tanks. and training personnel. and small agitated tanks. Closed cellular glass insulation is normally resistant to insulation fires because it is difficult for the ethyleneamines to saturate these materials and also difficult for air to contact the product. and oxygen from the atmosphere may be absorbed by the amines. DETA. A 300 series stainless steel is often specified for pumps.Storage and Handling Ethyleneamines react with many other chemicals. carbon dioxide. In some cases. Proper selection of materials of construction for ethyleneamine service is essential to ensure the integrity of the handling system and to maintain product quality. However. but the products will pick up iron and discolor badly. even at ambient temperature. sometimes rapidly and usually exothermically. and either smoldering or a flame may be observed. dumped filter cake. transfer lines. certain grades of these materials may be acceptable in some storage applications. heavier ethyleneamines without noticeable impact on product quality. If this cannot be tolerated. nitrogen oxides. Carbon steel with baked phenolic lining is acceptable for storage of many pure ethyleneamines. inert atmosphere (such as low CO2-containing nitrogen) will minimize this sort of degradation. like many other combustible liquids. Corrosion is not extreme (<0. any of these media contaminated with ethyleneamines should be washed with water to remove the amines. copper and copper-bearing alloys are unacceptable for all ethyleneamine service. This may lead to low levels of byproducts and increase the color of the product. consistent with local and federal regulations.g. dedicated processing equipment is recommended. Storage under a dry. Nonmetallic equipment is not normally used for ethyleneamine service. it may not always prove suitable as a replacement material. self-heating of ethyleneamines may occur by slow oxidation in other absorbent or high-surface-area media. Also.. watersaturated containers. heating coils.

in certain concentrations. Tank vents and safety devices are also susceptible to fouling by solid amine carbamates formed by the reaction of the amines with carbon dioxide. even in areas where routine processing is nonaqueous. heavier ethyleneamines may be stored at elevated temperatures (40-60°C) to ease inplant handling by lowering the viscosity. Storage at elevated temperatures can cause vapors “breathing” from the tank to contain significant concentrations of product. Ethyleneamines are typically maintained above their freezing points which may require storage above ambient temperatures (particularly EDA and PIP). contact Dow at the numbers on the back of this booklet and request our Ethyleneamines Storage and Handling Brochure and/or a technical contact who will discuss specific questions about acceptable materials of construction and storage practices. contaminants can lower the onset of rapid exothermic thermal decomposition (for example. vent lines and safety devices. 35 .The amines do not present any unusual flammability problem at ordinary temperatures. Vent units require periodic inspection to verify that fouling is not occurring and to ensure that seals are functioning properly to exclude air from the tank. may be found in the Material Safety Data Sheets. Hydrate problems are usually avoided by insulating and heat tracing equipment to maintain a temperature of at least 50°C. solid amine hydrates may form. Health Effects Information on health effects and their management. This information is of a general nature. although the amines are water-soluble. as well as recommended safety procedures. Vent fouling can be reduced by using nitrogen blankets on storage tanks to exclude atmospheric CO2. which can be a nuisance in handling. Additionally. All amine vents should be routed to a safe location and “smoking vents” routed to water scrubbers to capture the vapors. At elevated temperatures some product breakdown may be observed in the form of ammonia and the formation of lower and higher molecular weight species. Additionally. Also. As commercially pure materials. contact Dow at the numbers on the back of this booklet. which are updated as new information becomes available. This degradation increases in rate as the temperature and/or time increases. vent units and relief devices may be steam-traced to maintain 160°C. For additional information. For the latest Material Safety Data Sheets on ethyleneamines. Water cleanup of ethyleneamine equipment can result in hydrate problems. ethyleneamines exhibit good temperature stability. Hydrates can plug processing equipment. Warm water cleanup can reduce the extent of the problem. EDA has the lowest flash point (Tag Closed Cup): 43°C (110°F). which causes the carbamates to decompose. mineral acids contamination). Testing for thermal stability is suggested whenever ethyleneamines are mixed with other materials. In addition.

Nonacclimated domestic sewage microorganisms used as seed.86 1.86 1. DETA. ASTM.86 1.28 1. EDA. 17th ed. Natural acclimation in a wastewater treatment plant or in the general environment would be expected to increase the rate and extent of biodegradation for the related compounds.68 1.94 1.54 Nitrogenous Calc. Several amines. and AEP. The nitrogenous oxygen demand is calculated based on nitrogen being oxidized to nitrate by nitrifying bacteria.84 1. Ecological Fate and Effects of Ethyleneamines Theoretical Oxygen Demand. 2. and Standard Methods techniques.49 1. Bacterial inhibition tests indicate that none of these amines tested should be inhibitory to conventional wastewater treatment processes at expected discharge levels of less than 500 mg/L. (3) The measured biooxidation as a percent of the total carbonaceous and nitrogenous oxygen demand (sum of calculated carbonaceous and nitrogenous ThOD values) is presented for Days 5. while the nitrogen converts to and remains as ammonia.33 1. 36 .64 1.13 1. 65% Aminoethylpiperazine Aminoethylethanolamine Carbonaceous Meas. (COD) 1. (ThOD) mg/mg(1) Product Evaluated Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. TETA. (1989). Aquatic toxicity measurements showed only moderate toxicity for most of the tested amines. Public Health Assoc.75 — — 1. Calculated value based on oxygen required to oxidize the chemical to carbon dioxide and water. except for EDA and AEEA. 1. and 20.55 1.48 1.93 1. Biodegradation was measured by the riversimulating 20-day biochemical oxygen demand (BOD) test using nonacclimated microorganisms.69 — 1. which rapidly biodegraded.63 Calc. 10.Ecological Fate and Effects Dow has conducted a series of laboratory studies on the biodegradation and ecological effects of these amines. The impact of acclimation on the rate and extent of biodegradation is shown by the EDA and DETA acclimated seed data. showed more toxicity to Daphnia magna with LC50 values ranging from 5 to 40 mg/L.. (2) Measured in dilution bottle biochemical oxygen demand test published in Standard Methods. These studies were conducted by procedures which follow the EPA.88 1. The biooxidation values are calculated as percentage ratio of BOD and ThOD (BOD/ThOD x 100).50 1. The data presented in the following table show that the amines biodegrade slowly.23 (1) Measured by Chemical Oxygen Demand (COD) procedure published in Standard Methods for the Examination of Water and Wastewater. with the exception of EDA/DETA studies which used acclimated seed.

or cosmetic until the user has determined the suitability and legality of the use. medical device. and customers. you should obtain available product safety information and take necessary steps to ensure safety of use. 37 . it is the user’s responsibility to determine that this information is appropriate and suitable under current. (5) Fathead minnows and Daphnia magna bioassays were conducted using procedures published by EPA and ASTM. or cosmetic. Dow requests that the customer read. Since government regulations and use conditions are subject to change. medical device. understand. mg/L Aquatic Toxicity (5) LC50. (6) Biooxidation values for EDA and DETA are taken from tests with acclimated microorganisms. you should review our latest Material Safety Data Sheets and ensure that the use you intend can be accomplished safely. drug. The 95% confidence limits (95% CL) are shown in parentheses. % biooxidation Total Carbonaceous(2) Days 5/10/20 68/100/100 A36(6)/A45(6)/A70(6) <5/<5/<5 A23(6)/A46(6)/A70(6) 3/4/9 4/7/12 <5/<5/<5 <10/<10/<10 2/4/7 2/64/90 —/—/— —/—/— —/—/— —/—/— —/—/— —/—/— 1/37/53 >5000 680 — — 4600 1400 >5000 25/37/78 1000 Nitrogenous(3) Days 5/10/20 Bacterial (4) Inhibition IC50. contractors. No nitrification was measured in the acclimated systems. or in a product or process in which it may contact a food.Product Safety When considering the use of any Dow products in a particular application. No chemical should be used as or in a food. The customer should furnish the information in these publications to its employees. mg/L 48-hour 96-hour Daphnia magna Fathead Minnow 5 (4-6) 17 (15-19) 40 (35-50) — — 90 (80-110) 36 (25-50) 110 (90-130) 210 (190-230) 260 (220-310) 330 (280-400) 310 — 720 (640-800) 560 (500-620) 515 (470-560) (4) Determined by turbidity/growth procedures where the median inhibition concentration (IC50) is measured after 16 hours of incubation with sewage microorganisms. drug. and request that t hey do the same. Biochemical Oxygen Demand(2). and comply with the information contained in this publication and the current Material Safety Data Sheet(s). For Material Safety Data Sheets and other product safety information. Before handling any other products mentioned in the text. or any other users of the product(s). applicable laws and regulations. contact Dow at the numbers on the back of this booklet.

Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for modifying urea-formaldehyde resins used as the basic polymer and as a resin to anchor coatings to the substrate in the manufacture of food-packaging cellophane.FDA Status Dow provides the following FDA Status Summary for the convenience of our customers.180 176. Modifier for urea-formaldehyde and melamine-formaldehyde resins for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with fatty. Polyamides formed by reaction with dimerized vegetable oil acids for use as components of food-packaging adhesives. Polyamides from dimerized vegetable oils for use as adjuncts for epoxy resins.105 175.390 176. Catalyst for epoxy resins and component of polyamides for use in zinc-silicon dioxide matrix coatings.320 173.25 173. crusher.1010 177. crusher. aqueous. sulfanilic acid. Catalyst for epoxy resins and component of polyamides for use in xylene-formaldehyde resins condensed with 4.1210 177.320 175.170 176.180 176. Urea-formaldehyde resins chemically modified with polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food.5 wt% of the rubber product. Accelerator in vulcanization of rubber articles intended for repeated use. Modifier for urea-formaldehyde resins for use as the basic polymer in cellophane and as a resin to anchor coatings to substrate. not to exceed 1. 175. Formulation of defoaming agents used in the manufacture of paper and paperboard prior to and during the sheet forming operation. Modifier for amino resins used as a component of the coated and uncoated food-contact surface of paper and paperboard in contact with fatty. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane.300 Preparation of ion-exchange membranes used in the processing of grapefruit juice.2600 178.20 173. aqueous. Catalyst for epoxy resins used as the food contact surface of paper and paperboard in contact with fatty.170 176.180 176.180 176.1200 177.3120 38 . aqueous. Polyamides from vegetable oil acids and sebacic acid for use in side seam and can-end cements. as a modifier for melamine-formaldehyde resins used in cellophane. and other listed amines. Additive in the production of animal glue.300 177.210 176. Modifier for urea-formaldehyde and melamine-formaldehyde resins used as the basic polymer in resinous and polymeric coatings on a metal substrate. or holding food. and dry food. Component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food (as a crosslinking agent in polymerization).0 ppm based on the weight of raw cane or beets processed. Catalyst for epoxy resins and component of polyamides for use in making closures with sealing gaskets.300 175. and as a resin to anchor coatings to substrate.380 175. Component in an antimicrobial formulation used in cane sugar and beet sugar mills. Adjuvant in the preparation of slimicides used as antimicrobial agents to control slime in the manufacture of paper and paperboard. transporting.105 175.4’-iso-propylidenediphenol epichlorohydrin epoxy resins.170 176. applied to the sugar mill grinding.300 175. it is the responsibility of the user of an ethyleneamine as a Direct or Indirect Food Additive to read and understand any applicable FDA regulations in Title 21 of the Code of FDA Regulation Ethylenediamine 21 CFR Permitted Uses 173.170 176. However.1200 177. at a level not to exceed 0. and dry food. Polyamide-epichlorohydrin resins prepared by reacting adipic acid or other acids with diethylenetriamine to form a basic polyamide and further reaction of the polyamide with other materials to form water-soluble thermosetting resins for use in the manufacture of paper and paperboard. Crosslinker with epichlorohydrin to make ion-exchange resins used in the processing of food. and dry food.0 ppm based on the weight of raw cane processed.300 175.180 176. Component in an antimicrobial formulation used in cane sugar mills. Modifier for melamine-formaldehyde resins for use as the basic polymer in cellophane. and/or diffusor systems at a maximum level of 2.1200 177. Catalyst activator in semirigid and rigid acrylic and modified acrylic plastics. Catalyst and crosslinking agent for epoxy resins used in resinous and polymeric coatings applied as a continuous film or enamel over a metal substrate or applied as a continuous film or enamel to any suitable substrate provided that the coating serves as a functional barrier between the food and the substrate and is intended for repeated food-contact use.5 wt% based on the monomers.1200 177. Component of adhesives used in articles intended for packaging. applied to the sugar mill grinding.180 176. and/or diffusor systems at a maximum level of 1.

Federal Regulations (21 CFR) to determine any limitations or restrictions on the proposed use. and FDA-compliant. safe. Diethylenetriamine (EDA) Triethylenetetramine (DETA) ✔ ✔ Tetraethylenepentamine (TETA) ✔ Aminoethylethanolamine (TEPA) ✔ (AEEA) ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ 39 . it is the responsibility of the user to determine that any such use is suitable. Furthermore.

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